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1-(6-Chloropyridazin-3-yl)piperidin-4-amine → 2-ter-Butyl-4-{[1-(6-chloropyridazin-3-yl)piperidin-4-yl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxide

HRID 2422087
Notes
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Reaction equation

HRID 2422087 reaction equation
[C:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2].[Cl:20][C:21]1[N:26]=[N:25][C:24]([N:27]2[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]2)=[CH:23][CH:22]=1>CC#N>[C:1]([N:5]1[C:9](=[O:10])[C:8]([NH:33][CH:30]2[CH2:31][CH2:32][N:27]([C:24]3[N:25]=[N:26][C:21]([Cl:20])=[CH:22][CH:23]=3)[CH2:28][CH2:29]2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 64164231-(6-Chloropyridazin-3-yl)piperidin-4-amineHCID 672426272-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 115185352-ter-Butyl-4-{[1-(6-chloropyridazin-3-yl)piperidin-4-yl]amino}-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 27%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

2-tert-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (0.450 g, 1.50 mmol), 1-(6-chloropyridazin-3-yl)piperidin-4-amine (0.487 g, 1.95 mmol) and TEA (0.456 g, 4.50 mmol) was dissolved in dry MeCN (15 ml) and heated in a microwave reactor at 120° C. for 30 mins. The reaction mixture was evaporated and the residue was diluted with EtOAc (150 ml) and washed with water (500 ml). The organic phase was dried over MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography using a 60:40→50:50 mixture of heptane and EtOAc as eluant, to give the title compound (0.191 g, 27%). 1H NMR (500 MHz, CDCl3): δ 7.55-7.50 (m, 2H), 7.47-7.43 (m, 3H), 7.15 (d, 1H), 6.81 (d, 1H), 5.20 (d, 1H), 4.11-4.05 (m, 2H), 3.22-3.13 (m, 1H), 2.60-2.52 (m, 2H), 1.80-1.73 (m, 2H), 1.72 (s, 9H), 1.41-1.32 (m, 2H); 13C NMR (125 MHz, CDCl3): δ 159.5, 158.6, 147, 133.8, 131.6, 130, 128.8, 128.7, 125, 115.4, 107.3, 61.6, 50, 43.8, 31.6, 27.6.

Workup

  1. customThe reaction mixture was evaporated
  2. additionthe residue was diluted with EtOAc (150 ml)
  3. washwashed with water (500 ml)
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography
  8. additiona 60:40→50:50 mixture of heptane and EtOAc as eluant

Sources & evidence

ORD record
ord-87fe71ce128d4decae59a4d9a4af1607
Source dataset
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07960380B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes